I'm not really sure what might make a Caesar salad worth $19, but I do know that it wasn't what I was served for lunch at Manny's. While I'm not going to fuss about finding a few aging, discolored leaves in the salad bar at Shakey's Pizza, it's the sort of thing I wouldn't expect to see at a top steak house operated by one of the savviest local restaurant groups (Parasole, which owns Chino Latino, Figlio, and Salut, among others). I was glad I'd asked for the anchovies—two flat fillets laid across the lettuce heap like they'd stretched out for a nap—because the anemic salad dressing lacked any of its characteristic pungency. The chicken breast was dry, the accompanying Parmesan crisp tasted as if it had picked up stale refrigerator odors, and a hunk of garlic bread had the texture of a pumice stone. I had to beg my friend not to take off his shoe and start rubbing his calluses.

Serves me right, you say, for going to a steak place and ordering a salad. Well, you know what, I did order a steak—and it was worse than the salad. Picture one of those hot, moist towels doled out at Japanese restaurants. If you rolled one up, coated it with pepper, and took a bite—well, that's the best way I can think to describe the peppered bar steak. (It probably didn't help that the steak came without a trace of its promised blue cheese.)

As I ate a few forkfuls of steak, I tried to remember the magic number of times nutritionists say you're supposed to chew each bite before swallowing. Forty-six...forty-seven...forty-eight...the meat barely yielded. Eventually, I was forced to swallow it like a flavorless wad of chewing gum.

This was not supposed to happen at Manny's. Not the institution that's won "best steak house" more times than any other in town. And especially not since Manny's moved from its dank, windowless digs in the Hyatt to its tony new space in the W Hotel. In adding breakfast and lunch service, had the restaurant lost its luster? I felt like I'd overpaid to be underwhelmed. Like I'd been suckered. Like I'd eaten at a tourist trap.

At just the right moment, the waiter returned to clear the plates. (At least the service was still perfect.) "Want the damage?" he asked.

"I dunno," I joked. "How bad is it?"

"At lunch it's not that bad. At dinner, that's when we wallop you."

A WEEK LATER, wallop me they did: My dinner check at Manny's was more than twice as fat as the lunch one, but this time, at least, it felt worth every penny. There's nothing like a stiff drink, a juicy steak, and a towering dessert to make you feel like you live in the richest country in the world. And when you whip out the plastic to pay the damage, it hurts in a good way, like a trip through the birthday spanking machine.

The Manny's difference begins at the host stand, which is staffed not by awkward, low-paid teenagers but by management-level employees who take their service as seriously as concierges—yet still know how to crack a joke. One night I watched a woman tell the host that her husband was parking the car and would be arriving shortly. "You want me to show him to your table, or another one?" he quipped. He then led her past Manny's infamous bull painting (the beast's prominent manhood was the subject of a recent C.J. gossip column) and into the formal dining room with its sleek black booths and brown-and-white cattle hides tacked on the wall.

Manny's waiters sell dinners the way they have for decades, wheeling one of the mobile meat/fish counters up to each table. They present the raw steaks on plastic-wrapped plates, flipping them about so deftly you'd think they were about to launch into a juggling routine. The live lobster, for its part, simply pinches its claws and sneers. While getting up close and personal with the raw product feels a little indiscreet, it is nice to see exactly what you're going to get, and to have the chance to ask questions—none of which ever seem to stump the waiters.

That's because the staff at Manny's are at the top of the food chain: competent, confident, unflappable. As they should be, I suppose, considering they can make five-plus bucks just by carrying one steak to the table. The jobs are so coveted, management says, that typically one opens up every two to three years.

The diners at Manny's aren't nearly as exclusive a bunch. At one table, a woman might be wearing her glitziest gown and biggest bling, while at another, a guy looks like he might have pulled his Rush concert T-shirt out of the dirty clothes heap. One night, a man sipped a cognac and entertained a flock of fashion models, while two tables away a guy old enough to know better had to be asked to take off his cap. Though Manny's is a popular spot for birthday and anniversary dates, the meat-cart traffic jams make it seem less romantic than rowdy. Seats on banquettes are cozy enough to encourage cross-party chatter. I watched two groups talk so long they bonded enough to clink glasses.

Perhaps they were celebrating their steaks, which Manny's has been buying from the same Kansas City purveyor for about 20 years. They're cooked precisely and served simply: Most arrive with just a parsley garnish, except for the filet mignon, which arrives with a side of béarnaise sauce. The tenderloin may be ordered in either a 14-ounce portion or a 10-ounce one "for the ladies," a description that seems a little outdated, particularly since I watched a couple split a 40-ounce steak and saw the woman match the man bite for bite. This massive, bone-in rib eye—otherwise known as the "bludgeon of beef," because it looks precisely like a prehistoric murder weapon—is, in my mind, the restaurant's signature steak (it may also be ordered in a more modest 26-ounce version). Its crust is slightly salty, flecked with crispy shards of char, and the meat takes on the bright, acidic flavors enhanced by dry aging. This is a steak for a carnivore's carnivore.

The steaks go well with wine, of course, and Manny's has an extensive list of American reds, from a smooth, by-the-glass house cabernet to a slew of those biblically named big bottles, including a $2,000, nine-liter Kenwood "Artist Series." My favorite pre-steak appetizer is the Caprese salad made with burrata, the grand slam of Italian soft cheeses. Burrata is basically a cream-filled ball of fresh mozzarella, which combines a lovely, soft, ricotta-like texture with a musty, tangy, goat-cheese-like flavor. When ordering a side, I recommend the hash browns: They're a textbook execution, a crisp, golden disk the size of a Frisbee—three people barely finished half. For groups, these excessive portions, which our waiter tactfully described as "a little over the top," are certainly reasonable. But on a table for two, an order of broccoli looks like a small forest, the loaded mashed potatoes like a snow-capped mountain. And how many calories might there be in the $15 brownie, a dark, dense chocolate block the size of a car battery topped with whipped cream and ice cream, doused with chocolate and caramel sauces, and sprinkled with pecans?

I suppose that's the point, though: The audacity of Manny's is precisely what makes it fun. That was probably part of the reason Manny's wasn't nearly as thrilling at lunch or breakfast. The lobster eggs Benedict and blueberry-mascarpone stuffed French toast were certainly tasty, but how often do two people blow $65 on breakfast?

Inside Manny's, diners seem insulated from these questions of excess. It was only when I stood out on the Foshay's 30th-floor observation deck that my worries blew in with the crisp fall breeze: Would we soon feel the consequences of spending too much money and indulging in too much rich food? Wilbur Foshay himself had scarcely opened the doors on his magnificent building before going bankrupt in the 1929 stock market crash. I took in the view of the glittering skyscape and wondered how long such decadence might last.